Taken mostly from a good post here http://www.enrise.com/2012/12/git-and-vagrant-in-a-windows-environment/ Assumes you have latest cygwin and virtualbox installed.
Cygwin need svn and bash Install other deps
svn --force export http://apt-cyg.googlecode.com/svn/trunk/ /bin/ chmod +x /bin/apt-cyg apt-cyg install make ruby curl git bsdtar ssh
Get Vagrant 1.1.0 dev from git (once this is stable then this step is not needed).
git clone https://github.com/mitchellh/vagrant.git cd vagrant
Update pull request for cygwin fix from here https://github.com/mitchellh/vagrant/pull/1366
curl https://github.com/mitchellh/vagrant/pull/1366.patch | git am
Install gem so deps are install then rake install to update to dev version with patches applied
gem install vagrant rake install
Add VBOX_USER_HOME
export VBOX_USER_HOME=`pwd`/.VirtualBox/
Add symlink to VBoxManage
ln '/cygdrive/c/Program\ Files/Oracle/VirtualBox/VBoxManage.exe' /usr/local/bin/VBoxManage
Use vagrant
vagrant box add lucid32 http://files.vagrantup.com/lucid32.box vagrant init lucid32 vagrant upYou May get an error when starting up. This is because the Virtual box guest additions need to be installed so the directory can be mounted
vagrant ssh sudo apt-get install virtualbox-guest-addition